3,4-anhydro-1,2-O-isopropylidene-α-L-tagatopyranose | 161642-83-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧环庚烷
• 英文名称: 3,4-anhydro-1,2-O-isopropylidene-α-L-tagatopyranose
• 英文别名: (1'R,4S,5'S,6'R)-2,2-dimethylspiro[1,3-dioxolane-4,2'-3,7-dioxabicyclo[4.1.0]heptane]-5'-ol
• CAS: 161642-83-7
• 化学式: C₉H₁₄O₅
• 分子量: 202.207
• InChiKey: GVWCBASRIAMGEM-SZACMFPPSA-N

物化性质

• 沸点：
  318.9±42.0 °C(predicted)
• 密度：
  1.37±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  60.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3,4-anhydro-1,2-O-isopropylidene-α-L-tagatopyranose 在 sodium hydroxide 、 硫酸 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 54.0h， 生成 L-Fructose
  参考文献：
  名称：

  Application of a phase transfer reaction to the synthesis of l-fructose

  摘要：

  L-Fructose was prepared in five steps from L-sorbose (1). 1,2-O-Isopropylidene-alpha-L-sorbopyranose (2), prepared from 1, was selectively tosylated using phase transfer catalysis to give 1,2-O-isopropylidene-3-O- (p-tolylsulfonyl)-alpha-L-sorbopyranose (3). Formation of a 3,4-anhydro ring, followed by its base-catalyzed opening to effect overall inversion of configuration at both C-3 and C-4 gave 1,2-O-isopropylidene-alpha-L-fructopyranose (5), which was deacetonated to yield L-fructose (6).

  DOI：

  10.1016/0008-6215(94)00255-e
• 作为产物：
  描述：

  L-sorbopyranose 在 sodium hydroxide 、 四丁基硫酸氢铵 、 copper(II) sulfate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 7.42h， 生成 3,4-anhydro-1,2-O-isopropylidene-α-L-tagatopyranose
  参考文献：
  名称：

  Application of a phase transfer reaction to the synthesis of l-fructose

  摘要：

  L-Fructose was prepared in five steps from L-sorbose (1). 1,2-O-Isopropylidene-alpha-L-sorbopyranose (2), prepared from 1, was selectively tosylated using phase transfer catalysis to give 1,2-O-isopropylidene-3-O- (p-tolylsulfonyl)-alpha-L-sorbopyranose (3). Formation of a 3,4-anhydro ring, followed by its base-catalyzed opening to effect overall inversion of configuration at both C-3 and C-4 gave 1,2-O-isopropylidene-alpha-L-fructopyranose (5), which was deacetonated to yield L-fructose (6).

  DOI：

  10.1016/0008-6215(94)00255-e

文献信息

• Application of a phase transfer reaction to the synthesis of l-fructose
  作者：Yonas Gizaw、James N. BeMiller

  DOI：10.1016/0008-6215(94)00255-e

  日期：1995.1

  L-Fructose was prepared in five steps from L-sorbose (1). 1,2-O-Isopropylidene-alpha-L-sorbopyranose (2), prepared from 1, was selectively tosylated using phase transfer catalysis to give 1,2-O-isopropylidene-3-O- (p-tolylsulfonyl)-alpha-L-sorbopyranose (3). Formation of a 3,4-anhydro ring, followed by its base-catalyzed opening to effect overall inversion of configuration at both C-3 and C-4 gave 1,2-O-isopropylidene-alpha-L-fructopyranose (5), which was deacetonated to yield L-fructose (6).